((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol | 183722-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol
• 英文别名: [(2R,3S)-3-[(4-methoxyphenyl)methoxy]oxan-2-yl]methanol
• CAS: 183722-51-2
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: FUVWMMSUSMPDFJ-UONOGXRCSA-N

物化性质

• 沸点：
  389.5±32.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol 在 草酰氯 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 (2R,3S)-2-vinyltetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  cis-3,4-Dichlorocyclobutene as a Versatile Synthon in Organic Synthesis. Rapid Entry into Complex Polycyclic Systems with Remarkably Stereospecific Reactions We thank Drs. D. H. Huang and G. Siuzdak for their assistance with NMR spectroscopy and mass spectrometry, respectively. This work was financially supported by the National Institutes of Health (USA) and The Skaggs Institute for Chemical Biology, a postdoctoral fellowship from the Skaggs Institute for Research (to V.G.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

  摘要：

  DOI：

  10.1002/1521-3773(20011203)40:23<4441::aid-anie4441>3.0.co;2-i
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 在 D(+)-10-樟脑磺酸 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 15.0h， 生成 ((2R,3S)-3-(4-methoxybenzyloxy)tetrahydro-2H-pyran-2-yl)methanol
  参考文献：
  名称：

  cis-3,4-Dichlorocyclobutene as a Versatile Synthon in Organic Synthesis. Rapid Entry into Complex Polycyclic Systems with Remarkably Stereospecific Reactions We thank Drs. D. H. Huang and G. Siuzdak for their assistance with NMR spectroscopy and mass spectrometry, respectively. This work was financially supported by the National Institutes of Health (USA) and The Skaggs Institute for Chemical Biology, a postdoctoral fellowship from the Skaggs Institute for Research (to V.G.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.

  摘要：

  DOI：

  10.1002/1521-3773(20011203)40:23<4441::aid-anie4441>3.0.co;2-i

文献信息

• Synthesis of Novel Pyran <font>β</font>-Amino Acid and 5,6-Dihydro-2H-pyran <font>β</font>-aminoxy Acid from Carbohydrate Derivatives
  作者：Gattu Sridhar、Marumamula Hanumaiah、Gangavaram V. M. Sharma

  DOI：10.1080/00397911.2015.1043018

  日期：2015.8.3

  Abstract Synthesis of two new amino acids, containing pyran rings, is reported from carbohydrate derivatives. The cis-3-amino-pyran-2-carboxylic acid (cis-APyC) was prepared from (R)-glyceraldehyde derivative, using nucleophilic substitution reaction for pyran ring formation. Similarly, the trans-3-aminoxy-5,6-dihydro-2H-pyran-2-carboxylic acid (trans-AmPyC) was prepared from diacetone glucose (DAG)

  摘要 报道了从碳水化合物衍生物合成两种含有吡喃环的新氨基酸。顺-3-氨基-吡喃-2-羧酸（cis-APyC）由（R）-甘油醛衍生物制备，使用亲核取代反应形成吡喃环。类似地，反式-3-氨氧基-5,6-二氢-2H-吡喃-2-羧酸（反式-AmPyC）由双丙酮葡萄糖（DAG）制备，使用闭环复分解（RCM）反应形成环。图形概要
• Stereoselective Synthesis of Medium-Sized Cyclic Ethers: Application of <i>C</i>-Glycosylation Chemistry to Seven- to Nine-Membered Lactone-Derived Thioacetals and Their Sulfone Counterparts
  作者：Yuto Suga、Haruhiko Fuwa、Makoto Sasaki

  DOI：10.1021/jo4025545

  日期：2014.2.21

  Stereoselective synthesis of α,α′-substituted medium-sized cyclic ethers has been achieved by means of nucleophilic substitution of the corresponding lactone-derived thioacetals and their sulfone counterparts. Nucleophilic substitution of medium-sized lactone-derived thioacetals could be achieved efficiently either by (i) activation with NIS/TMSOTf in the presence of allyltrimethylsilane or TMSCN or

  已经通过相应的内酯衍生的硫缩醛及其砜对应物的亲核取代，实现了α，α'-取代的中型环状醚的立体选择性合成。中型内酯衍生的硫缩醛的亲核取代可以通过（i）在烯丙基三甲基硅烷或TMSCN存在下用NIS / TMSOTf活化，或（ii）氧化成相应的砜，然后用适当的有机金属物质处理来有效地实现作为二乙烯基锌或二甲基（2-苯基乙炔基）铝。有趣的是，发现立体化学结果在很大程度上取决于底物的局部结构。在某些情况下，在过渡状态下形成的gauche空间相互作用被认为是所观察到的非对映选择性的原因。
• Convergent synthesis of the FGHI ring segment of yessotoxin
  作者：Isao Kadota、Hirokazu Ueno、Yuki Sato、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2005.10.136

  日期：2006.1

  A convergent synthesis of the FGHI ring segment of yessotoxin was achieved via the intramolecular allylation of an α-chloroacetoxy ether and subsequent ring-closing metathesis.

  通过α-氯乙酰氧基醚的分子内烯丙基化和随后的闭环易位，实现了耶毒素的FGHI环段的收敛合成。
• Selective cleavage of primary MPM ethers with TMSI/Et3N
  作者：Isao Kadota、Yuji Yamagami、Naoya Fujita、Hiroyoshi Takamura

  DOI：10.1016/j.tetlet.2009.05.084

  日期：2009.8

  A useful method for the selective cleavage of primary MPM ethers by using TMSI/Et3N is described. Other protective groups such as secondary MPM ethers, silyl ethers, and benzylidene acetal were stable under the reaction conditions. (C) 2009 Elsevier Ltd. Ail rights reserved.
• cis-3,4-Dichlorocyclobutene as a Versatile Synthon in Organic Synthesis. Rapid Entry into Complex Polycyclic Systems with Remarkably Stereospecific Reactions We thank Drs. D. H. Huang and G. Siuzdak for their assistance with NMR spectroscopy and mass spectrometry, respectively. This work was financially supported by the National Institutes of Health (USA) and The Skaggs Institute for Chemical Biology, a postdoctoral fellowship from the Skaggs Institute for Research (to V.G.), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Novartis, Pfizer, and Schering Plough.
  作者：K. C. Nicolaou、Juan A. Vega、Georgios Vassilikogiannakis

  DOI：10.1002/1521-3773(20011203)40:23<4441::aid-anie4441>3.0.co;2-i

  日期：2001.12.3